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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:24 UTC
HMDB IDHMDB01355
Secondary Accession NumbersNone
Metabolite Identification
Common NameParathion
DescriptionParathion is a highly toxic cholinesterase inhibitor that is used as an acaricide and as an insecticide.
Structure
Thumb
Synonyms
ValueSource
Diethyl P-nitrophenyl thiophosphateChEBI
Diethyl parathionChEBI
DNTPChEBI
Ethyl parathionChEBI
O,O-Diethyl O-(4-nitrophenyl) thiophosphateChEBI
O,O-Diethyl O-(P-nitrophenyl) thiophosphateChEBI
O,O-Diethyl O-P-nitrophenyl phosphorothioateChEBI
Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) esterChEBI
ThiophosChEBI
Diethyl P-nitrophenyl thiophosphoric acidGenerator
Diethoxy-(4-nitrophenoxy)-sulphanylidene-$l^{5}-phosphaneGenerator
O,O-Diethyl O-(4-nitrophenyl) thiophosphoric acidGenerator
O,O-Diethyl O-(P-nitrophenyl) thiophosphoric acidGenerator
O,O-Diethyl O-P-nitrophenyl phosphorothioic acidGenerator
Phosphorothioate, O,O-diethyl O-(4-nitrophenyl) esterGenerator
AlkronHMDB
AlleronHMDB
American cyanamid 3422HMDB
AphamiteHMDB
Aqua 9-parathionHMDB
AraloHMDB
BladanHMDB
BladenHMDB
CorothionHMDB
CorthioneHMDB
DanthionHMDB
Deoxynucleoside 5'-triphosphateHMDB
Diethyl 4-nitrophenyl phosphorothionateHMDB
Diethyl O-P-nitrophenyl phosphorothioateHMDB
Diethyl O-P-nitrophenyl phosphorothioic acidHMDB
Diethyl P-nitrophenyl thionophosphateHMDB
Diethyl para-nitrophenol thiophosphateHMDB
Diethyl-P-nitrophenyl monothiophosphateHMDB
DiethylparathionHMDB
Drexel parathion 8EHMDB
DurathionHMDB
EcatoxHMDB
EthlonHMDB
Ethyl parathion (O,O-diethyl-O-P-nitrophenylthiophosphate)HMDB
EtilonHMDB
FoliclalHMDB
FolidolHMDB
Folidol e e 605HMDB
Folidol e605HMDB
Folidol oilHMDB
FosfermoHMDB
FosfernoHMDB
fosferno 50HMDB
FosfexHMDB
FosfiveHMDB
FosovaHMDB
FosternHMDB
FostoxHMDB
GearphosHMDB
GenithionHMDB
KolphosHMDB
KypthionHMDB
Lethalaire g-54HMDB
LirothionHMDB
MurfosHMDB
NiranHMDB
NitrostygmineHMDB
Niuif-100HMDB
NourithionHMDB
O,O-Diethyl-O-(P-nitrophenyl)thionophosphateHMDB
Oleofos 20HMDB
OleoparapheneHMDB
OleoparathionHMDB
OMS 19HMDB
OrthophosHMDB
P-Nitrophenol O-ester with O,O-diethylphosphorothioateHMDB
P-Nitrophenol O-ester with O,O-diethylphosphorothioic acidHMDB
PACHMDB
PacolHMDB
PanthionHMDB
ParadustHMDB
ParamarHMDB
Paramar 50HMDB
ParaphosHMDB
ParatheneHMDB
Parathion-eHMDB
ParawetHMDB
ParthionHMDB
Penncap eHMDB
Pestox plusHMDB
PethionHMDB
PhoskilHMDB
PhosphemolHMDB
PhosphenolHMDB
PhosphorothioateHMDB
Phosphorothioic acidHMDB
Phosphorothioic acid O,O-diethyl-O-(4-nitrophenyl) esterHMDB
PhosphostigmineHMDB
RhodiasolHMDB
RhodiatoxHMDB
RhodiatroxHMDB
SelephosHMDB
Sixty-three special e.cHMDB
SoprathionHMDB
Stabilized ethyl parathionHMDB
StathionHMDB
StrathionHMDB
SulfosHMDB
Super rodiatoxHMDB
T-47HMDB
ThiomexHMDB
Thionspray no.84HMDB
Thiophos 3422HMDB
TiofosHMDB
VapophosHMDB
ViranHMDB
VitrexHMDB
Chemical FormulaC10H14NO5PS
Average Molecular Weight291.261
Monoisotopic Molecular Weight291.033029765
IUPAC NameO,O-diethyl O-4-nitrophenyl phosphorothioate
Traditional NameO,O-diethyl O-4-nitrophenyl phosphorothioate
CAS Registry Number56-38-2
SMILES
CCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3
InChI KeyInChIKey=LCCNCVORNKJIRZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Thiophosphate triester
  • Organic thiophosphoric acid or derivatives
  • Thiophosphoric acid ester
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point6.1 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.011 mg/mLNot Available
LogP3.83Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 mg/mLALOGPS
logP3.76ALOGPS
logP3.32ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area73.51 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity72.69 m3·mol-1ChemAxon
Polarizability26.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a74-8940000000-4bf55c77de23f747eb80View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0687-68.721 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022574
KNApSAcK IDNot Available
Chemspider ID13844817
KEGG Compound IDC06604
BioCyc IDPARATHION
BiGG IDNot Available
Wikipedia LinkParathion
NuGOwiki LinkHMDB01355
Metagene LinkHMDB01355
METLIN IDNot Available
PubChem Compound991
PDB IDNot Available
ChEBI ID27928
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bohn G, Rucker G, Luckas KH: [Mass spectrometric and gaschromatographic detection of parathione in autopsy material after murder by poisoning]. Z Rechtsmed. 1971;68(1):45-52. [5547745 ]
  2. SALAMA S, EL-SHIHY A, IBRAHIM HH, KODSY A: THE ACTION OF PARATHIONE ON THE C.N.S. J Egypt Med Assoc. 1963;46:500-8. [14066548 ]
  3. Youssef SH, el-Sayed MG, Atef M: Influence of gentamicin and rifamycin on toxicity and biotransformation of methyl parathione in rats. Dtsch Tierarztl Wochenschr. 1987 Apr 8;94(4):203-5. [3297603 ]
  4. Innocenti A, Supuran CT: Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of alpha- but not of beta-, gamma- and zeta-carbonic anhydrases. Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12. doi: 10.1016/j.bmcl.2010.08.110. Epub 2010 Aug 26. [20833546 ]
  5. Kawahara K, Tanaka A, Yoon J, Yokota A: Reclassification of a parathione-degrading Flavobacterium sp. ATCC 27551 as Sphingobium fuliginis. J Gen Appl Microbiol. 2010 Jun;56(3):249-55. [20647682 ]
  6. Lotz W, Fasske E: [Pneumonitis with fatal pulmonary fibrosis (Hamman-Rich syndrome) due to parathion-(E-605-) poisoning]. Rofo. 1986 May;144(5):536-41. [3012677 ]
  7. SALAMA S, EL-SHISHY A, IBRAHIM HH: THE ACTION OF PARATHIONE ON THE CIRCULATORY & RESPIRATORY SYSTEMS. J Egypt Med Assoc. 1963;46:240-62. [14065272 ]
  8. Mueller RF, Hornung S, Furlong CE, Anderson J, Giblett ER, Motulsky AG: Plasma paraoxonase polymorphism: a new enzyme assay, population, family, biochemical, and linkage studies. Am J Hum Genet. 1983 May;35(3):393-408. [6305189 ]

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular weight:
56687.095
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP4B1
Uniprot ID:
P13584
Molecular weight:
58990.64
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Molecular weight:
59085.45
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
General function:
Involved in monooxygenase activity
Specific function:
Has a potential importance for extrahepatic xenobiotic metabolism.
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Molecular weight:
55816.205
General function:
Involved in monooxygenase activity
Specific function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular weight:
57610.165
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2A7
Uniprot ID:
P20853
Molecular weight:
56424.735
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP1A1
Uniprot ID:
A0N0X8
Molecular weight:
58164.8
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0
Molecular weight:
55729.9